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Media type:
E-Article
Title:
Toward the Synthesis of Tetrazino‐tetrazine 1,3,6,8‐Tetraoxide (TTTO): An Approach to Non‐annulated 1,2,3,4‐Tetrazine 1,3‐Dioxides
Contributor:
Klenov, Michael S.;
Anikin, Oleg V.;
Churakov, Aleksandr M.;
Strelenko, Yurii A.;
Fedyanin, Ivan V.;
Ananyev, Ivan V.;
Tartakovsky, Vladimir A.
Published:
Wiley, 2015
Published in:
European Journal of Organic Chemistry, 2015 (2015) 28, Seite 6170-6179
Language:
English
DOI:
10.1002/ejoc.201500923
ISSN:
1434-193X;
1099-0690
Origination:
Footnote:
Description:
AbstractA novel approach for the synthesis of 6‐(tert‐butyl‐NNO‐azoxy)‐5‐methylthio‐1,2,3,4‐tetrazine 1,3‐dioxide (1) was developed. This compound is likely to be a precursor of tetrazino‐tetrazine 1,3,6,8‐tetraoxide. The synthetic strategy consists of four steps: a synthesis of bis(tert‐butyl‐NNO‐azoxy)methane, coupling of the latter with dimethyl nitrodithioimidocarbonate to give N‐nitroimine 3, O‐alkylation of the latter to O‐alkylated nitroenamine and its reaction with BF3·Et2O to afford tetrazine 1,3‐dioxide 1. An X‐ray diffraction study of 1 was accomplished.